Water → Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

HRID 495176Notes

Reaction equation

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.[Br:20]N1C(=O)CCC1=O.O>CN(C)C=O>[CH3:14][O:13][CH2:12][O:11][C:9]1[C:8]([Br:20])=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:10]=1

Participants

Conditions

Temperature: 4 °C

Procedure

Methyl 3,5-bis(methoxymethoxy)phenylacetate (43 g, 0.16 mol) obtained in Example 1, Step 1 was dissolved in N,N-dimethylformamide (0.68 L). After the solution was cooled to 4° C., N-bromosuccinimide (28 g, 0.16 mol) was added thereto, followed by stirring for 3 hours, while the temperature of the reaction mixture was raised to room temperature. To the reaction mixture was added water (0.50 L), and the mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/2, 0.40 L×4). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL) and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2) to obtain a quantitative yield of methyl 3,5-bis(methoxymethoxy)-2-bromophenyl-acetate.

Workup

temperaturewas raised to room temperature
extractionthe mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/2, 0.40 L×4)
washThe organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationfollowed by concentration under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2)

Sources & evidence

ORD record: ord-fd841cbea225467c8ba294a186da3e15
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538224B2

Reaction notes

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